EP4285724A2 - Liquid acetyl radicals generator composition - Google Patents
Liquid acetyl radicals generator composition Download PDFInfo
- Publication number
- EP4285724A2 EP4285724A2 EP23203617.8A EP23203617A EP4285724A2 EP 4285724 A2 EP4285724 A2 EP 4285724A2 EP 23203617 A EP23203617 A EP 23203617A EP 4285724 A2 EP4285724 A2 EP 4285724A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- organic solvent
- composition
- liquid
- mixture
- acetylcaprolactam
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000007788 liquid Substances 0.000 title claims abstract description 28
- 239000000203 mixture Substances 0.000 title claims description 96
- -1 perhydroxyl ions Chemical class 0.000 claims abstract description 58
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims abstract description 26
- QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 239000012964 benzotriazole Substances 0.000 claims description 8
- 239000002736 nonionic surfactant Substances 0.000 claims description 8
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000000249 desinfective effect Effects 0.000 claims description 6
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 claims description 5
- 238000005260 corrosion Methods 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 claims description 4
- WGKZYJXRTIPTCV-UHFFFAOYSA-N 2-butoxypropan-1-ol Chemical compound CCCCOC(C)CO WGKZYJXRTIPTCV-UHFFFAOYSA-N 0.000 claims description 4
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical group COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 4
- 238000002791 soaking Methods 0.000 claims description 4
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 241000228245 Aspergillus niger Species 0.000 claims description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 2
- 241000222122 Candida albicans Species 0.000 claims description 2
- 240000001817 Cereus hexagonus Species 0.000 claims description 2
- 241000194029 Enterococcus hirae Species 0.000 claims description 2
- 241000991587 Enterovirus C Species 0.000 claims description 2
- 241000186367 Mycobacterium avium Species 0.000 claims description 2
- 241000187495 Mycobacterium terrae Species 0.000 claims description 2
- 241001263478 Norovirus Species 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 2
- 241000191967 Staphylococcus aureus Species 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229940095731 candida albicans Drugs 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 241000701161 unidentified adenovirus Species 0.000 claims description 2
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000645 desinfectant Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- NRYLEVTUQMJPMG-UHFFFAOYSA-N C(C)(C)O.N1N=NC2=C1C=CC=C2 Chemical compound C(C)(C)O.N1N=NC2=C1C=CC=C2 NRYLEVTUQMJPMG-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004637 bakelite Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001839 endoscopy Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- ODBPOHVSVJZQRX-UHFFFAOYSA-M sodium;[2-[2-[bis(phosphonomethyl)amino]ethyl-(phosphonomethyl)amino]ethyl-(phosphonomethyl)amino]methyl-hydroxyphosphinate Chemical compound [Na+].OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)([O-])=O ODBPOHVSVJZQRX-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
Definitions
- the present invention relates to a new acetyl radicals generator composition particularly intended for preparing peracetic acid-based disinfectant compositions.
- Anioxyde 1000 A particularly effective solution for such an application is marketed by the Applicant under the name Anioxyde 1000 and is disclosed in patent application WO 00/53011 A1 .
- This product is composed of two distinct liquid compositions: an oxygen generator liquid base comprising hydrogen peroxide, on the one hand, and a liquid acetyl radicals generator comprising N-acetylcaprolactam solubilized in isopropanol, on the other hand.
- an oxygen generator liquid base comprising hydrogen peroxide
- a liquid acetyl radicals generator comprising N-acetylcaprolactam solubilized in isopropanol
- the Applicant is to be credited with having found, as a result of extensive research, the source of these stability problems. Indeed, it is particularly the isopropanol that is used as solvent that has a negative effect on the stability of the N-acetylcaprolactam.
- the invention firstly relates to a liquid acetyl radicals generator composition comprising N-acetylcaprolactam and an organic solvent, characterized in that the organic solvent is selected from propylene glycol ethers.
- the use of a propylene glycol ether instead of isopropanol allows the shelf life of the liquid acetyl radicals generator composition to be significantly increased.
- the composition according to the invention is preferably isopropanol free, and even aliphatic alcohol free in general.
- the term "propylene glycol ether" within the scope of the invention comprises monopropyl glycol ethers, dipropylene glycol ethers, tripropylene glycol ethers and their mixtures.
- the organic solvent is selected from C1 to C4 linear or branched alkyl or alkoxy propylene glycol ethers, C1 to C4 linear or branched alkyl or alkoxy dipropylene glycol ethers, C1 to C4 linear or branched alkyl or alkoxy tripropylene glycol ethers and their mixtures, more preferably from dipropylene glycol monomethyl ether, monopropylene glycol mono-n-butyl ether, dipropylene glycol mono-n-butyl ether (butoxypropanol), tripropylene glycol monomethyl ether and their mixtures.
- a particularly significant increase in the shelf life has been obtained with tripropylene glycol monomethyl ether.
- the N-acetylcaprolactam content of the acetyl radicals generator composition is advantageously from 30 % to 80 %, preferably from 40 % to 70 %, more preferably from 50 % to 65 % and more preferably approximately 60 % relative to the total weight of the composition.
- the organic solvent content of the acetyl radicals generator composition is advantageously from 10 % to 60 %, preferably from 20 % to 50 %, more preferably from 25 % to 40 % and more preferably from 30 % to 35 % relative to the total weight of the composition.
- the liquid acetyl radicals generator composition according to the invention can further comprise one or more surfactants.
- the one or more surfactants can be selected from non-ionic, anionic, amphoteric or cationic surfactants, with non-ionic surfactants being preferred.
- the one or more non-ionic surfactants particularly can be selected from alkoxylated and alkylpolyglucoside non-ionic surfactants.
- the alkoxylated non-ionic surfactants are advantageously selected from alkoxylated fatty alcohols, preferably ethoxylated and/or propoxylated, particularly polyalkoxylated fatty alcohols in which the polyalkoxylated part is composed of an OE-OP (ethylene oxide-proplyene oxide) copolymer block, and their mixtures.
- Commercial examples of such surfactants are those from the Genapol ® EP range marketed by Clariant (Muttenz, Switzerland), such as, for example, Genapol ® EP 2584 (mixture of C 12 C 15 polyalkoxylated alcohols (8OE, SOP).
- the surfactant advantageously is a surfactant with 100 % active material, i.e. water free.
- the non-ionic surfactant content in the acetyl radicals generator composition according to the invention advantageously is from 1 % to 10 %, preferably from 2 % to 7 %, more preferably approximately 5 % by weight relative to the total weight of the composition.
- the acetyl radicals generator composition according to the invention can further comprise an anti-corrosion agent such as benzotriazole, for example.
- an anti-corrosion agent such as benzotriazole
- benzotriazole had a negative influence on the stability of the composition according to the invention. It is for this reason that it is preferably benzotriazole free.
- the acetyl radicals generator composition according to the invention can further comprise one or more coloring agents or color indicators.
- the acetyl radicals generator composition according to the invention is particularly useful in combination with a liquid perhydroxyl ions generator composition. Therefore, the invention also relates to a kit for preparing a disinfectant composition containing peracetic acid, the kit comprising:
- the liquid perhydroxyl ions generator composition advantageously contains from 1 % to 7 %, preferably from 2 % to 5 %, more preferably from 2.5 % to 3.5 % and even more preferably approximately 3 % by weight relative to the total weight of the composition.
- the liquid perhydroxyl ions generator composition advantageously is an aqueous solution of hydrogen peroxide.
- the liquid perhydroxyl ions generator composition can further comprise stabilizing agents, particularly pH regulators, for stabilizing it over time while avoiding the decomposition of the hydrogen peroxide during storage.
- stabilizing agents can be selected, for example, from mineral and organic bases such as, for example, alkali hydroxides, such as potassium or sodium hydroxide, and alkanolamines, such as monoethanolamine, diethanolamine and triethanolamine.
- the liquid perhydroxyl ions generator composition can further comprise anti-corrosion agents.
- Suitable anti-corrosion agents particularly comprise phosphates, phosphonates, phosphoric esters and triazole derivatives such as benzotriazole.
- the perhydroxyl ions generator composition can further comprise one or more additive(s), such as stabilizing agents like, for example, anti-oxidant agents or anti-UV agents. It can also comprise a coloring agent or colored indicator. This is of particular interest in the event that the acetyl radicals generator composition according to the invention does not contain coloring or color indicator.
- the invention further relates to a method for preparing a disinfectant composition containing peracetic acid, in which:
- the disinfectant composition that is thus obtained is particularly useful for disinfecting, particularly by soaking, surgical and medical instruments and equipment. Therefore, the invention also relates to the use of the kit for preparing a disinfectant composition obtained according to the invention and to the disinfectant composition according to the method of the invention for disinfecting, particularly by soaking, surgical and medical instruments and equipment.
- the term "surgical and/or medical instruments and equipment” as used in the present application is to be broadly understood to be referring to the medical devices and all the other articles that are used in the medical, dental, pharmaceutical and veterinary fields that require cleaning with aqueous detergents prior to reuse. It particularly comprises surgical instruments, endoscopic equipment and echography probes, for example, transoesophageal probes.
- N-acetylcaprolactam The stability of the N-acetylcaprolactam in the various compositions was assessed using an accelerated ageing test at 50 °C. Sample preservation conditions: 250 ml glass bottle, Bakelite plug placed in an oven set to a temperature of 50 °C without controlled hygrometry.
- Table 2 ACL content (% by weight relative to the total weight) I1 I2 I3 I4 I5 EC T0 days 50 °C 60 60 60 60 60 60 60 T7 days 50 °C 59.76 59.91 60.29 60.09 60.99 56.49
- EXAMPLE 3 assessment of the microbiological activity of a disinfectant composition prepared with an acetyl radicals generator composition according to the invention
- a disinfectant composition was prepared by mixing 100 g of a hydroxyl radicals generator composition comprising (3.0 % hydrogen peroxide, 0.05 % sodium perborate tetrahydrate and 0.0075 % Dequest 2066 (Italmatch Chemicals), with the percentages being expressed by weight relative to the total weight of the hydroxyl radicals generator composition), with 0.82 g of the composition I15 being assessed for its microbiological performance against various strains in clean conditions according to the standards listed in table 5, with a contact time of 5 minutes. For comparison purposes, the same tests were performed with Anioxyde ® 1000 solution prepared according to the instructions.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
- The present invention relates to a new acetyl radicals generator composition particularly intended for preparing peracetic acid-based disinfectant compositions.
- In a hospital environment, some surgical and medical instruments or equipment such as, for example, surgical instruments or endoscopy equipment, require high-level disinfection. This disinfection is often carried out using soaking baths, in which the instruments and equipment are immersed.
- A particularly effective solution for such an application is marketed by the Applicant under the name Anioxyde 1000 and is disclosed in patent application
WO 00/53011 A1 - In addition to allowing fast and effective extemporaneous preparation of peracetic acid, this system allows full disinfection in five minutes. However, Anioxyde® 1000 has a major disadvantage. N-acetylcaprolactam is not in fact stable during the time in solution. The lifetime of the acetyl radicals generator is thus only 12 months.
- Therefore, a requirement exists for a liquid acetyl radicals generator composition for preparing a liquid peracetic acid-based disinfectant composition with a better lifetime compared to the prior art.
- The Applicant is to be credited with having found, as a result of extensive research, the source of these stability problems. Indeed, it is particularly the isopropanol that is used as solvent that has a negative effect on the stability of the N-acetylcaprolactam.
- Therefore, the invention firstly relates to a liquid acetyl radicals generator composition comprising N-acetylcaprolactam and an organic solvent, characterized in that the organic solvent is selected from propylene glycol ethers.
- Surprisingly, the use of a propylene glycol ether instead of isopropanol allows the shelf life of the liquid acetyl radicals generator composition to be significantly increased. Thus, the composition according to the invention is preferably isopropanol free, and even aliphatic alcohol free in general. The term "propylene glycol ether" within the scope of the invention comprises monopropyl glycol ethers, dipropylene glycol ethers, tripropylene glycol ethers and their mixtures. Preferably, the organic solvent is selected from C1 to C4 linear or branched alkyl or alkoxy propylene glycol ethers, C1 to C4 linear or branched alkyl or alkoxy dipropylene glycol ethers, C1 to C4 linear or branched alkyl or alkoxy tripropylene glycol ethers and their mixtures, more preferably from dipropylene glycol monomethyl ether, monopropylene glycol mono-n-butyl ether, dipropylene glycol mono-n-butyl ether (butoxypropanol), tripropylene glycol monomethyl ether and their mixtures. A particularly significant increase in the shelf life has been obtained with tripropylene glycol monomethyl ether.
- The N-acetylcaprolactam content of the acetyl radicals generator composition is advantageously from 30 % to 80 %, preferably from 40 % to 70 %, more preferably from 50 % to 65 % and more preferably approximately 60 % relative to the total weight of the composition.
- The organic solvent content of the acetyl radicals generator composition is advantageously from 10 % to 60 %, preferably from 20 % to 50 %, more preferably from 25 % to 40 % and more preferably from 30 % to 35 % relative to the total weight of the composition.
- The liquid acetyl radicals generator composition according to the invention can further comprise one or more surfactants. The one or more surfactants can be selected from non-ionic, anionic, amphoteric or cationic surfactants, with non-ionic surfactants being preferred. The one or more non-ionic surfactants particularly can be selected from alkoxylated and alkylpolyglucoside non-ionic surfactants. The alkoxylated non-ionic surfactants are advantageously selected from alkoxylated fatty alcohols, preferably ethoxylated and/or propoxylated, particularly polyalkoxylated fatty alcohols in which the polyalkoxylated part is composed of an OE-OP (ethylene oxide-proplyene oxide) copolymer block, and their mixtures. Commercial examples of such surfactants are those from the Genapol® EP range marketed by Clariant (Muttenz, Switzerland), such as, for example, Genapol® EP 2584 (mixture of C12C15 polyalkoxylated alcohols (8OE, SOP). With N-acetylcaprolactam being sensitive to hydrolysis, the surfactant advantageously is a surfactant with 100 % active material, i.e. water free.
- The non-ionic surfactant content in the acetyl radicals generator composition according to the invention advantageously is from 1 % to 10 %, preferably from 2 % to 7 %, more preferably approximately 5 % by weight relative to the total weight of the composition.
- The acetyl radicals generator composition according to the invention can further comprise an anti-corrosion agent such as benzotriazole, for example. However, the inventors have observed that benzotriazole had a negative influence on the stability of the composition according to the invention. It is for this reason that it is preferably benzotriazole free.
- The acetyl radicals generator composition according to the invention can further comprise one or more coloring agents or color indicators.
- The acetyl radicals generator composition according to the invention is particularly useful in combination with a liquid perhydroxyl ions generator composition. Therefore, the invention also relates to a kit for preparing a disinfectant composition containing peracetic acid, the kit comprising:
- in a first container, a liquid acetyl radicals generator composition as defined above; and
- in a second container, a liquid perhydroxyl ions generator composition comprising hydrogen peroxide.
- The liquid perhydroxyl ions generator composition advantageously contains from 1 % to 7 %, preferably from 2 % to 5 %, more preferably from 2.5 % to 3.5 % and even more preferably approximately 3 % by weight relative to the total weight of the composition.
- The liquid perhydroxyl ions generator composition advantageously is an aqueous solution of hydrogen peroxide.
- The liquid perhydroxyl ions generator composition can further comprise stabilizing agents, particularly pH regulators, for stabilizing it over time while avoiding the decomposition of the hydrogen peroxide during storage. These stabilizing agents can be selected, for example, from mineral and organic bases such as, for example, alkali hydroxides, such as potassium or sodium hydroxide, and alkanolamines, such as monoethanolamine, diethanolamine and triethanolamine.
- The liquid perhydroxyl ions generator composition can further comprise anti-corrosion agents. Suitable anti-corrosion agents particularly comprise phosphates, phosphonates, phosphoric esters and triazole derivatives such as benzotriazole.
- The perhydroxyl ions generator composition can further comprise one or more additive(s), such as stabilizing agents like, for example, anti-oxidant agents or anti-UV agents. It can also comprise a coloring agent or colored indicator. This is of particular interest in the event that the acetyl radicals generator composition according to the invention does not contain coloring or color indicator.
- When the acetyl radicals generator composition according to the invention is mixed with a perhydroxyl ions generator composition as described above, the N-acetylcaprolactam reacts with the hydrogen peroxide in a perhydrolysis reaction and thus generates peracetic acid. Therefore, the invention further relates to a method for preparing a disinfectant composition containing peracetic acid, in which:
- a liquid acetyl radicals generator composition is provided as defined above, particularly contained in a first container;
- a liquid perhydroxyl ions generator composition is provided as defined above, particularly contained in a second container; and
- the acetyl radicals generator composition and the perhydroxyl ions generator composition are mixed.
- The disinfectant composition that is thus obtained is particularly useful for disinfecting, particularly by soaking, surgical and medical instruments and equipment. Therefore, the invention also relates to the use of the kit for preparing a disinfectant composition obtained according to the invention and to the disinfectant composition according to the method of the invention for disinfecting, particularly by soaking, surgical and medical instruments and equipment. The term "surgical and/or medical instruments and equipment" as used in the present application is to be broadly understood to be referring to the medical devices and all the other articles that are used in the medical, dental, pharmaceutical and veterinary fields that require cleaning with aqueous detergents prior to reuse. It particularly comprises surgical instruments, endoscopic equipment and echography probes, for example, transoesophageal probes.
- The invention now will be described using non-limiting embodiments of the invention.
- List of abbreviations:
- ACL: N-acetylcaprolactam;
- DPM: dipropylene glycol monomethyl ether (Arcosolv® DPM);
- DPnB: dipropylene glycol mono-n-butyl ether (Arcosolv® DPnB);
- PnB: monopropylene glycol mono-n-butyl ether (Arcosolv® PnB);
- TPM: tripropylene glycol monomethyl ether (Dowanol® TPM);
- PM1: 1-methoxy-2-propanol (methoxypropanol).
- Four liquid acetyl radicals generator compositions according to the invention composed of N-acetylcaprolactam and a propylene glycol ether (I1 - I5) were prepared and compared to an acetyl radicals generator composition according to
WO 00/53011 A1 Table 1 Composition (% by weight/total weight) I1 I2 I3 I4 I5 EC1 N-actvlcaprolactam 60 60 60 60 60 60 Isopropanol 40 DPM 40 PM1 40 DPnB 40 PnB 40 TPM 40 - The stability of the N-acetylcaprolactam in the various compositions was assessed using an accelerated ageing test at 50 °C. Sample preservation conditions: 250 ml glass bottle, Bakelite plug placed in an oven set to a temperature of 50 °C without controlled hygrometry.
- The test results are summarized in table 2 below.
Table 2 ACL content (% by weight relative to the total weight) I1 I2 I3 I4 I5 EC T0 days 50 °C 60 60 60 60 60 60 T7 days 50 °C 59.76 59.91 60.29 60.09 60.99 56.49 - These results clearly show that the use of a propylene glycol ether allows the stability of the acetyl radicals generator composition to be increased compared to a composition according to
WO 00/53011 A1 - Eight liquid acetyl radicals generator compositions (I6 - I13) according to the invention were prepared and their stability assessed and compared to a composition with isopropanol (EC). Their compositions are provided in table 3.
Table 3 Composition (% by weight/total weight) EC2 I6 I7 I8 I9 I10 I11 Isopropanol 30.3 Benzotriazole 3.7 3.7 3.7 3.7 Genapol EP 2584 Coloring agent N-acetylcaprolactam 60 60 60 60 60 60 60 DPM 30.3 34 DPnB 30.3 34 PnB TPM PM1 30.3 34 Composition (% by weight/total weight) I12 I13 I14 I15 Isopropanol Benzotriazole 3.7 3.7 Genapol EP 2584 Coloring agent N-acetylcaprolactam 60 60 60 60 DPM DPnB PnB 30.3 34 TPM 30.3 34 PM1 - The stability of the N-acetylcaprolactam in the various compositions was assessed using the accelerated ageing test at 50 °C described in example 1. The test results are summarized in table 4 below.
Table 4 ACL content (% by weight relative to the total weight) EC2 I6 I7 I8 I9 I10 I11 T0 days 50 °C 60 60 60 60 60 60 60 T7 days 50 °C 50.1 53.8 59.4 54.91 59.06 53.25 59.55 T15 days 50 °C 44.9 49.7 58.3 51.71 58.53 49.23 58.20 ACL content (% by weight relative to the total weight) I12 I13 I14 I15 T0 days 50 °C 60 60 60 60 T7 days 50 °C 53.29 59.79 53.37 60.18 T15 days 50 °C 50.34 59.00 51.48 59.92 - These results show that all the compositions according to the invention have improved stability over time compared to the sample containing isopropanol (EC2) and thus an acceptable shelf life (lifetime). When the composition does not contain benzotriazole, its stability is further improved. The best result is obtained for the composition with TPM.
- A disinfectant composition was prepared by mixing 100 g of a hydroxyl radicals generator composition comprising (3.0 % hydrogen peroxide, 0.05 % sodium perborate tetrahydrate and 0.0075 % Dequest 2066 (Italmatch Chemicals), with the percentages being expressed by weight relative to the total weight of the hydroxyl radicals generator composition), with 0.82 g of the composition I15 being assessed for its microbiological performance against various strains in clean conditions according to the standards listed in table 5, with a contact time of 5 minutes. For comparison purposes, the same tests were performed with Anioxyde® 1000 solution prepared according to the instructions.
Table 5 Microbial reduction Standard Strain Invention Anioxyde® 1000 EN 13727+A2 (December 2015) Pseudomonas aeruginosa > 5 Log > 5 Log Staphylococcus aureu > 5 Log > 5 Log Enterococcus hirae > 5 Log > 5 Log EN 14348 (June 2015) Mycobacterium terrae > 4 Log > 4 Log Mycobacterium avium > 4 Log > 4 Log EN 13624 (November 2013) Candida albicans > 4 Log > 4 Log Aspergillus niger > 4 Log > 4 Log EN 13704 (April 2002) 5Log B. subtilis > 5 Log > 5 Log B. cereus > 5 Log > 5 Log EN 14476 + A1 (October 2015) 4Log Poliovirus > 4 Log > 4 Log Adenovirus > 4 Log > 4 Log Norovirus > 4 Log > 4 Log - These results show that a disinfectant composition prepared on the basis of an acetyl radicals generator composition according to the invention allows a full disinfection spectrum to be obtained in 5 minutes. This performance is the same level as that obtained for the reference product, Anioxyde® 1000.
-
- 1. Liquid acetyl radicals generator composition comprising N-acetylcaprolactam and an organic solvent, characterized in that the organic solvent is selected from propylene glycol ethers.
- 2. Composition according to item 1, characterized in that the organic solvent is selected from dipropylene glycol monomethyl ether, monopropylene glycol mono-n-butyl ether, dipropylene glycol mono-n-butyl ether (butoxypropanol), tripropylene glycol monomethyl ether and their mixtures.
- 3. Composition according to item 2, characterized in that the organic solvent is tripropylene glycol monomethyl ether.
- 4. Composition according to any of the preceding items, characterized in that the N-acetylcaprolactam content is from 30 % to 80 % by weight relative to the total weight of the composition.
- 5. Composition according to any of the preceding items, characterized in that the solvent content is from 10 % to 60 % by weight relative to the total weight of the composition.
- 6. Composition according to any of the preceding items, characterized in that it further comprises a non-ionic surfactant.
- 7. Composition according to any of the preceding items, characterized in that it is benzotriazole free.
- 8. Kit for preparing a disinfectant composition containing peracetic acid, the kit containing:
- in a first container, a liquid acetyl radicals generator composition according to any of the preceding claims; and
- in a second container, a liquid perhydroxyl ions generator composition comprising hydrogen peroxide.
- 9. Method for preparing a disinfectant composition containing peracetic acid, wherein:
- an acetyl radicals generator composition is provided according to any of claims 1 to 7;
- a perhydroxyl ions generator composition is provided comprising hydrogen peroxide;
- the acetyl radicals generator composition and the perhydroxyl ions generator composition are mixed.
- 10. Use of a kit according to item 8 for disinfecting surgical and/or medical instruments and equipment.
- 11. Use of a disinfectant composition prepared according to the method of item 9 for disinfecting surgical and/or medical instruments and equipment.
Claims (15)
- A method of generating peracetic acid comprising:combining N-acetylcaprolactam, an organic solvent, and a liquid perhydroxyl ions generator to form a mixture; wherein the mixture comprises from 30% to 80% N-acetylcaprolactum; wherein the organic solvent comprises a propylene glycol ether; and wherein the mixture is free of aliphatic alcohol;generating peracetic acid.
- The method of claim 1, wherein the organic solvent is selected from dipropylene glycol monomethyl ether, monopropylene glycol mono-n-butyl ether (butoxypropanol), dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether and their mixtures.
- The method of claim 2, wherein the organic solvent is tripropylene glycol monomethyl ether.
- The method of any one of the preceding claims, wherein the liquid perhydroxyl ions generator comprises hydrogen peroxide.
- The method of any of the preceding claims, further comprising including a non-ionic surfactant in the combining step, preferably from 1% to 10% in the mixture.
- The method of any one of the preceding claims, further comprising including a stabilizing agent and/or anti-corrosion agent in the combining step.
- The method of claim 6, wherein the stabilizing agent comprises as an alkali hydroxide or an alkanolamine; and wherein the anti-corrosion agent comprises a phosphate, a phosphonate, a phosphoric ester, or a triazole derivative.
- The method of any of the preceding claims, wherein the mixture is benzotriazole free.
- The method of any of the preceding claims, wherein the N-acetylcaprolactam and the organic solvent are in a premix.
- Use of the peracetic acid generated according to any one of claims 1-7, the use comprising disinfecting.
- The use of claim 10, wherein surgical and/or medical instruments and equipment are disinfected.
- The use of claim 11, wherein the disinfecting is performed by soaking the surgical and/or medical instruments and equipment.
- The use of claim 10 or 11, wherein the surgical and/or medical instruments and equipment is medical, dental, pharmaceutical and/or veterinary instruments and equipment.
- The use of any one of claims 10-13, wherein a microbial population is reduced by greater than 4 Log.
- The use of claim 14, wherein the microbial population comprises Pseudomonas aeruginosa, Staphylococcus aureu, Enterococcus hirae, Mycobacterium terrae, Mycobacterium avium, Candida albicans, Aspergillus niger, B. subtilis, B. cereus, Poliovirus, Adenovirus, and/or Norovirus.
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FR1754507A FR3066362B1 (en) | 2017-05-22 | 2017-05-22 | LIQUID COMPOSITION GENERATING ACETYL RADICALS |
EP18729317.0A EP3629736B1 (en) | 2017-05-22 | 2018-05-22 | Liquid acetyl radicals generator composition |
PCT/US2018/033856 WO2018217723A1 (en) | 2017-05-22 | 2018-05-22 | Liquid acetyl radicals generator composition |
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ITVR20020062A1 (en) * | 2002-06-03 | 2003-12-03 | Andrea Pretto | ESTEMPORANEOUS PREPARATION OF ORGANIC PERIOXYACIDS STABLE OVER TIME |
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